Quinolin compounds and process of producing same.



UNITED STATES PATENT OFFICE.

ALEX B. DAVIS, OE INDIANAPOLIS, INDIANA, ASSIGNOR TO THE ELI LILLY AND COMPANY, OF INDIANAPOLIS, INDIANA, ACORPORATION OF INDIANA.

QUINOLIN COMPOUNDS AND PROCESS OF PRODUCING SAME.

No Drawing.

Specification of Letters Patent.

Patented May 26, 1914.

Application filed January 31, 1913. Serial No. 745,376.

' Same, of which the following is a specification.

My invention relates to compounds of the quinolin series and processes of producing them. 1

The compounds are all derivatives of (2) ortho oxy-phenyl-quinolin (4) carboxylic acid, which are made by the process of boiling together in molecular proportions in ab-' solute alcoholic solution, an -aromatic -alde hyde, an aromaticamm and-pyruvic acid.

The following hitherto; unknown" compounds have been prepared by'my method (2) ortho-oxy-phenyl (6) methyl-quinolin (4) carboxylic acid, b (2) ortho-oxy-phenyl 8) methyl-quinolin (4) carboxylic acid, (2 orthooxy-phenyl (7 methyl-quinolin (4) carboxylic acid, (2) ortho-oxy-phenyl (6) methoxy-quinolin (4) carboxylic acid, 2) ortho-oxy-phenyl- ('7 methoxy-quinolin(4 carboxylic acid, (2)

ortho oxyphenyl (8) methoxy-quinolin (4) carboxylic acid.

This new quinolin compound may be represented by the following formula are in which X is a radical takin the place of the hydrogen atom in one of te OH groups of the quinolin ring. 7

Esters of these acids may be obtained by known processes of esterification. For instance, the ethyl esters may be obtained by passing dry hydrochloric acid gas into solutions of the acids in absolute alcohol.

While all of the above compounds are of value, I wish especially to cover the first of the above list, namely (2) ortho-oxyhenyl- (6) methyl-quinolin (4:) carboxylic aci ,which can be obtained by boiling together in absolute alcoholic solution, equimolecular proportions of 'para-toluidin, salicyclic aldehyde and 'pyroracemic (pyruvic) acid for a number of hours, and allowing to crystallize.

In carrying out the process in detail, one may proceed as follows: In a vessel provlded with a refluxcondenser, .are placed 61 parts (by weight) of salicyclic aldehyde, and 44 parts of pyruvic acid, and to this mixture there is added an equal volume of absolute alcohol.

It is then heated to boilmg and in the course of 1} hr. 53.5 parts of para-toluidin in solution in an equal volume of absolute alcohol are allowed to flow in. The resulting mixture is boiled four-hours, and then set aside, when tlie quinolin compound crystallizes out, is filtered oil and recrystallized twice from 90% methyl alcohol. It then appears as yellow crystals melting at 95 C. The other members of the group are produced in much the same manner from the corresponding toluidins or anisidins,

What I claim is,

1. A quinolin compound having the following formula groups of the quinolin ring.

- 2. A quinolln compound consisting of (2) orthooxy-phenylmethy1-quinolin(4) carboxylic acid. i

' 3. A quinolin compound consisting of (2) ortho oxy phenyl (6) methyl quinolin- (4)carboxylic-acid. p

4. The process of producin a quinolin com ound which consists in boi ing together in a solute alcoholic solution equ niolecular proportions of para-toluidin, salicyclic aldehyde and pyruvic acid and then permitting the compound to crystallize. v 5. The process-of producing derivatives of (2) ortho oxy-phenylquinolin (4) carboxylic acid which consists in boiling together inabsolute alcoholic solution equimolecular proportions of salicyclic aldehyde, pyruvic acid and an equimolecular proportion of an aromatic amin suitable for formin a member of the group desired to be pro uced.

v i which X is a radical taking the place of the hydrogen atom: in one of the CHv 6. The process of producin a quinolin compound which consists in boi ing together salicyclic aldehyde, para-toluidin and pyru- Vic acid in equimolecular proportions in absolute alcoholic solution, permitting the resulting quinolin compound to crystallize out and then recrystallizing the product from alcohol,

In witness whereof, I- have hereunto set my hand and seal at Indianapolis, Indiana, 10 this twenty eighth day of January, A. D. nineteen hundred and thirteen.

ALEX B. DAVIS. [Ls] Witnesses:

FRANK R. ELDRED, W. SHOWALTER. 

